Squarespace: How to Grow a Company from $30k to $38M


“The things that made you successful in the past, don’t always make you successful in the future,” said Squarespace Founder and CEO Anthony Casalena to a packed room at StartUp Grind NY’s monthly fireside chat.

The web designer launched Squarespace in 2003, in his dorm room at the University of Maryland, where he was an engineering student. The impetus: his dismay with available CMS systems.  He did get his degree – and a $30k loan from his father to bring his innovative platform to life.

The company’s last reported earnings were more than $38 million.

For those unfamiliar with Squarespace, the company creates websites for small businesses and turning their ideas into modern, streamlined web destinations.  They’re also known for their attention to details, customer service and for delivering quality content.

They presently offer over 20 templates, which are optimized for tablet, mobile and desktop users.

Throughout his first three years in business, Casalena’s meticulous focus on relationship building was evident in everything he touched – and paid off.  As the sole employee, he drafted the site itself, solved customer issues, compiled orders, handled each phone call and answered every email, all of which added up to $25k in billings a week, $1 million in annual revenue, and doubling profits for three consecutive years, without the benefit of additional capital or staff support. A staff of 252 now work out of their sleek Soho loft ,which serves as the company’s headquarters. They also have an office in Dublin, Ireland and are opening a west coast office in Portland, Oregon.

When combing through portfolios of potential employees, Casalena admits to not having a precise formula when it comes to the hiring process.  “Interviewing is a flawed experience.  I want to see passion,” he said.

He illustrated why interviews are tiny windows into who a person truly is and how many managers and CEO’s begin to witness the emerging personality and work ethic of others only after they are given projects and expected to adhere to company standards.

Aside from talent and skills, other factors determine how far an employee will accelerate:  he or she must demonstrate commitment and be able to function without supervision.

“Am I going to meet this person once a month and feel confident that he or she is capable of not being managed or babysat?  Can this individual do their job without me holding their hand?”

Securing talent is a must for Casalena.  Squarespace powers more than 1.8 million websites and focuses on visual imagery, such as video enhancements, when creating the sites.  Only the company’s specialized teams can implement revisions or enhance tools into their website builder, unlike their competitors, where users can manipulate the sites themselves.  Any questions or conflicts customers may have are directed to guest relations, which operate on a 24/7 basis. All queries are addressed within an hour.

Casalena highlighted the four central tenets to his business, all of which contribute to raising brand awareness and fostering long-term success: alignment, judgment, community and technical ability.

It’s working. Casalena seems to have realized early on that he’s in a people business and he’s all about that. Which might explain why it is that his employees stay and his customers keep coming back.